Stupid Cupid
by Jeune Ecrivain
Summary: Jackson Stewart didn’t ask to fall in love with his sister’s best friend, but apparently, fate would hear none of it. What happens when a skateboarding incident prompts him to go out on a limb?
1. Chapter 1

**Stupid Cupid**

**By Jeune Ecrivain**

**Rating: T**

**Summary: Jackson Stewart didn't ask to fall in love with his sister's best friend, but apparently, fate would hear none of it. What happens when a skateboarding incident prompts him to go out on a limb?**

Jackson Stewart hated Cupid. He hated fate. He hated…whatever cosmic force had put him in this predicament. He didn't ask for this. He didn't ask to bond with his sister's best friend, but it happened. Somehow, whenever Lily Trescott was over and Miley Stewart was momentarily distracted for whatever reason, Lily always seemed to end up chatting idly with him. Whenever they were both undercover at one of Miley's concerts, there was something special about sharing the knowledge of pop star Hannah Montana's true identity as they often worked together to maintain secrecy. Soon, their chats weren't so idle anymore, and he found that Lily made keeping the Stewart family secret more adventurous and fun.

Jackson wanted to curse Oliver Oken, the two girls' mutual third best friend, for not occupying Lily enough himself when Miley wasn't around, but he knew it wasn't Oken's fault. Still, becoming friends with Lily wasn't that bad in and of itself. In fact, he enjoyed it. Apparently, though, fate didn't plan on being so kind as to leave it at that. Jackson would never forget that night when Lily had come over to watch a movie only to find out that Miley and Oliver had been delayed by an empty gas tank. So, he and Lily ended up channel surfing while they waited for the two to return with the goods from Blockbuster. Lily had happened upon something he wanted to watch further but she didn't, and the fight was on. Jackson remembered vividly the sensation of playfully wrestling, tickling, and chasing her. A climactic wrestling maneuver had put them nose-to-nose against a wall, and being the idiot he was, he had stopped to look at her long enough to realize for the first time just how beautiful she was. He had promptly yanked himself out of the compromising position, but he the sentiments that the incident had stirred within him still had not faded. Instead, they had only grown. The bond Jackson and Lily had developed prior to that moment combined with the realization of the latter's beauty yielded a very precarious result. That's right. Jackson Stewart was smitten with his sister's best friend, and it was driving him crazy! Cupid could've gone easy on him by making him fall for a girl who was his own age and not close friends with a family member, but instead the little winged archer had apparently decided to play a prank on him.

As Jackson chuckled mirthlessly at his situation, he almost didn't see the very girl who had captured his fancy limping up to the Stewart house, wincing with each step. His eyes widened attentively as he noticed her uneven gait, the gash on her leg, and the dirt on her face. Without thinking, he rushed out and met her on her way up to the front door. "What happened to you?" he asked in genuine concern.

She gave him the smallest of smiles before wincing again as she took another step. "Skateboarding competition," she answered gloomily. "I was this close to winning, and then Christine slammed her skateboard into mine and sent me flying off course. I ended up tumbling down this rocky hill while they just laughed!" Every two or three words, she winced in pain as she put weight on her injured leg.

Jackson couldn't take it anymore. He gripped her shoulders firmly, silently telling her to stop. She looked relieved but somewhat confused. Her confusion turned to outright surprise, however, when in one swift move he scooped her up into his arms. A yelp escaped her lips that Jackson inwardly couldn't help but find cute. "What are you doing?" she demanded as he proceeded to carry her into the house.

"I can't believe you walked all this way with your leg the way it is," was his only response. He bore her into the living room and set her own as gently as he could on the couch. He then went to the kitchen and pulled out a Ziploc bag. As he used the dispenser in the freezer to fill it with ice, he spoke on impulse. "Why do you put yourself through this kind of stuff?"

Lily shrugged. "I like skateboarding, I guess."

Jackson nodded as dampened a washcloth in the sink before heading over to where she sat. He looked at her, and he couldn't help but notice that she looked somewhat downcast. Pausing to give her a compassionate gaze, he knelt down in front if her. "Alright, let's rest that leg up here," he said as he gently lifted the injured limb and set her heel on the coffee table. Placing and holding the ice on her ankle with one hand, he raised the damp cloth with the other. Ever so lightly, he ran the cold rag down the length of the long cut on her calf. He was suddenly struck with the sensuality of it all as his fingers grazed in contact with the supple skin. He continued to rub her wound gently, and he fought the urge to stiffen nervously lest he cause her pain. When he finally allowed his eyes to meet hers, she looked thoughtful and a little downtrodden. "You alright, Lil?" he asked.

"Yeah, I'm fine," she said. As Jackson continued to clean her wound, Lily furrowed her brow slightly and looked at him with curiosity. She knew he wasn't nearly cold or inconsiderate enough to not at least try to ease her pain, but there was something about his behavior that went beyond simple compassion. She couldn't quite put her finger on it, but it was there. He wasn't even rubbing her leg. Instead, the cloth grazed her skin gracefully as his hand glided up and down her shin. He acted almost as if she was the most delicate thing in the world, and while the tomboy in her was repulsed by the sensation, she also found herself tempted to close her eyes in pleasure. She was seeing a side of Jackson she had never seen before, and she was strangely pleased by it.

Meanwhile, he slowly stopped washing the gash and placed the makeshift ice pack on her ankle. "So, they laughed at you, eh?" he said, doing his best to sound casual.

"Yeah," she confirmed indignantly. "Told me I should just take my klutzy butt on home and sell my skateboard."

"You don't deserve that," replied Jackson with a chuckle that nevertheless failed to mask the underlying sincerity. "You're the best skater I know."

Lily cocked her head. "You think so?"

"Totally," he answered. "Of course, I don't know many skaters, but I have a feeling you'd still be the best one I know. Even if by some wild chance you weren't, you're still an amazing girl overall." Jackson froze. Did he just say that out loud?

Fortunately, Lily didn't seem to notice as she just gave him a small smile and responded, "Really? How so?"

Jackson hesitated for a moment, but decided on a whim to take a chance. "Well, first of all, there's the way you keep Miley's secret. All you'd have to do is let the world know your best friend is the hottest pop star since Hilary Duff, and you're looking at instant popularity in school. But you don't. You stand by Miley and her secret identity. You jump through hoops to help her keep it a secret sometimes, and you never complain. You're a really loyal friend, Lily, and I really think that's great." He paused. "I also like how determined you are. If you have your mind set on something, you don't let anything get in your way. Kinda like Miley, only a little less annoying."

Lily giggled softly. "That's really sweet of you, Jackson. And here I thought I was just your sister's annoying best friend you sometimes hang out with because you have nothing better to do."

"I like hanging out with you," he blurted as he turned to look into her eyes. "You're more fun than most girls."

"Jackson, you're starting to creep me out," she chuckled. "When did you get so caring?"

He pouted. "You think I'm cold and heartless? I'm hurt," he said, feigning emotional pain. He then set the ice pack down and rose to his feet. Walking into the kitchen again, he paused and put his hands on his hips. "This is my own house, and I don't know where the bandages are kept," he observed with a self-derisive smirk.

Lily rolled her eyes. "You're pathetic," she teased. "Here, let me show you…" she moved to stand up and got halfway erect when a wave of pain hit her and she stumbled. Jackson wasted no time in rushing to her side just in time for her to fall quite literally into his arms. Reveling in the rush he got from her proximity, Jackson rubbed her back slightly, and unbeknownst to him, Lily felt the sudden urge to moan in pleasure. Her eyes widening at her own feelings, she moved to pull away. The subtle sensuality of their position proved too much for both of them as they both paused with their faces mere centimeters apart.

Perhaps drunk with sensation, Jackson threw caution to the wind and let his lips brush against Lily's. He felt her gasp softly, but to his surprise, she pulled away only a hair. A loaded pause followed before Lily leaned in ever so slowly and grazed his lips with hers as if testing the waters. She gradually relaxed and let her lips touch his more firmly, and Jackson followed suit. He broke away but a millimeter as he lowered both her and himself onto the couch. Once there, his lips found hers again, and there was no hesitation in her response. Lily's lips parted slightly, and Jackson took the invitation to deepen the kiss. He slipped his arms around her slim waist, exhilarated by the contact and the fact that she was letting him do this. Lily's arms, which were already draped around his neck from her fall, wrapped more tenderly around his collar. Lily herself was surprised how good it felt. The kiss grew more and more passionate until they finally broke for air.

"Jackson,…" Lily began, bewildered. "…did we really just do that?"

"Either that, or it's the most realistic dream I've ever had," Jackson replied.

Lily blushed crimson. "You dream about kissing me?"

Now it was Jackson's turn to blush, and that was all the answer Lily needed. Simultaneously intimidated by the fact that Jackson obviously had feelings for her and amused at how cute Jackson looked at that moment, she acted on impulse. Cupping his head in her hands, she captured his lips with hers once more and moaned softly as he kissed her back hungrily.


	2. Chapter 2

**Stupid Cupid**  
**By Jeune Ecrivain**  
**Rating: T**  
**Summary: Jackson Stewart didn't ask to fall in love with his sister's best friend, but apparently, fate would hear none of it. What happens when a skateboarding incident prompts him to go out on a limb?**

"Dad, I need your advice."

Robby Stewart resisted the temptation to roll his eyes. "Save it, son," he said. "Just tell me what you want the money for."

"Did it ever occur to you that sometimes I might actually need some man-to-man advice from my father?" Jackson replied indignantly.

"I suppose so," the elder Stewart shrugged. "But more often than not you just want something and you're just trying and failing miserably to be subtle about it."

"Well, this time it's different."

This caught Robby's attention, since Jackson's usual retort consisted of exaggerated protestations to the contrary. "Alright, I'll bite. What's up?"

"It's about a girl," his son responded somewhat sheepishly.

"Keep going."

"Well, I really like this girl. We've gotten to know each other pretty well, and we have a lot of fun together sometimes. She's not like a lot of girls, you know? She's a bit of a tomboy, but in a way that can be so feminine at the same time…if that makes any sense. And she's beautiful, smart, and funny."

"Sounds like you've got it bad. So what's the problem?"  
"Well, I kind of kissed her the other day, and…" Jackson began.

"And she didn't take it very well," Robby finished for him, or so he thought.

"No, actually she kissed me back. It was slow at first, but she eased into it pretty quick. But then we were interrupted, and I we haven't really had a chance to talk since," Jackson said, remembering when Miley had arrived home early from the hairdresser and almost caught him and Lily in what was quickly becoming a heated make-out session. "Things have been kind of awkward lately, and it's driving me crazy."

"Well, son, the best advice I can give you is to wait a while and give her some space for a few days, then try talking to her. You just sprung your feelings on her, and she might be trying to decide what she wants to do about it."

"There's more," Jackson said nervously. "This girl, she's…a little younger than me."

Robby cocked an eyebrow. "How much younger?"

"Two years."

The father shrugged. "Well, that's not too bad. The only issue there is how her parents might feel about her dating an older guy. But if you play it safe, I think you can convince 'em to give you a chance."

Jackson looked thoughtful for a moment (a rare sight). "You're probably right," he concluded.

"The important thing right now, though, is to talk to her," Robby reminded him before moving to get up from the couch he'd been sitting on.

"There's more," interrupted Jackson, sounding even more nervous now.

The father gave his son a look as he settled back into his seat. "How complicated does this get?"

"If only you knew," the son muttered before reasserting himself as best he could. "The thing is…she's a close friend of a relative."

Robby cocked an eyebrow for the second time in the conversation. "How close of a relative?"

Jackson scratched the back of his neck hesitantly. "Oh, pretty close, I'd say," he said vaguely.

The response that was on Robby's tongue was stopped short by a knock at the door to the patio. He turned to find Oliver Oken standing outside. "It's open," he said loudly.

Oliver slid the transparent door open. "Hey, is Miley here?" he asked.

"She's at the beach, Oken," answered Jackson.

"Thanks." Oliver turned to leave but turned back momentarily. "By the way, what'd you do to Lily? I've caught her giving you this weird look a couple times today."

"Thank you, Oken," replied Jackson, his voice dripping in sarcasm.

It hardly took a second for Robby to put two and two together. Jackson could practically see the lightbulb over his head as he turned back to face his son with an expression that said quite clearly _You have GOT to be kidding me_. "You kissed Trescott?!"

Jackson winced. "Maybe," he replied sheepishly.

"You kissed Lily?!" Oliver marveled.

Jackson threw his hands up in defeat. _Great. Why don't I just tell all of Malibu?_

Oliver blinked. "If something comes of this, could you let me know when you're gonna tell Miley?"

Jackson looked perplexed. "Why?"

"I just wanna see the look on her face!" Oliver grinned.

"Out!" Jackson commanded. "And not a word about this to Miley or it's your head. Got it?"

Oliver smirked before closing the door and walking away to find Miley. Robby was about to ask his son how in tarnation he ended up smitten with his sister's best friend when no sooner had Oliver disappeared than Lily herself walked up to the door looking somewhat apprehensive. She opened the door. "Hey, Mr. Stewart," she said, sounding a little surprised to see him but doing her best to sound cheerful. "Can I come in?"

"Sure, Lily," answered the elder Stewart as he threw the younger a sideways glance. "I'm going to go see what Miley's up to, but I'm sure Jackson can keep you company," he said. Feeling his son's glare on his back as he rose from the couch, Robby said softly and discretely to his son, "This could only happen to you," before excusing himself to look for his daughter.

As soon as Robby was out of earshot, Lily erupted. "You just had to kiss me, didn't you?!" she yelled.

Jackson knew that conversations like the one that was about to occur were never very predictable, but he definitely hadn't expected her to yell at him. "What? You kissed me back!" he protested.

"Exactly!" Lily replied as if it were obvious. "I was doing perfectly fine until you just had to go all romantic on me, swooping me up and nursing my leg like that! Now I have all these feelings that I never knew I had coming to the surface, and I don't know what to do about it!"

Despite his intimidation at Lily's mood, Jackson couldn't help but grin goofily. "You have feelings for me?"

She glared at him. "Yes! Thanks to you and that amazing kiss, my own blissful ignorance about how I really feel about my BEST FRIEND'S BROTHER is out the window!"

The goofy grin returned. "Amazing, huh?"

"Missing the point Jackson!" She took a few steps towards him and stopped. "On the list of awkward situations, having these kinds of feelings for your BEST FRIEND'S BROTHER is up HERE!" She stressed the point by waving her hand high above her head. "I don't even know why you wanted to kiss ME, of all people! I'm not even that pretty or anything!"

"Okay, first of all, you are beautiful," Jackson corrected her sternly. "Second of all, do you think I wanted this? I'm not any more at ease with this than you are! I didn't ask to feel this way about my LITTLE SISTER'S BEST FRIEND! But the truth is, Lily, nobody can help how they feel! I tried to get over you, but there's just something about you, Trescott! You're not like other girls. You're different…in a way that, for whatever reason, I just can't resist."

Lily stared at him, her irritation deflated. "You said I was beautiful," she said in awe.

Jackson's resolve also softened. "Now who's missing the point?" he teased.

"How do you do that?"

"Do what?"

Lily stepped slowly towards him, limping somewhat on her bandaged leg. "How can you be such a dork one minute and so sweet the next?"

He shrugged. "I have my moments."

All trace of irritation was now gone from her voice as she stepped closer still. "Why can't you have more of these 'moments'?" she said, trying to sound indignant.

"Maybe if you gave me a chance, I would," he retorted, drawing closer to her.

"Just do me a favor, okay?" Lily asked sincerely. "No more awkwardness. From now on, let's just be completely open and honest with each other about this."

"Deal."

"Good."

"Lily…"

"Yeah?"

"I want to kiss you."

The slightest pause preceded her response. "I want to kiss you, too," she whispered.

That was all Jackson needed to hear. He wrapped his arms gingerly around her waist and kissed her lips tenderly. He pulled away momentarily before it all became too much for him and he firmly captured her lips with his own. Her response was immediate. She parted her lips blatantly, and Jackson wasted little time in accepting the invitation. Her arms found their way around his neck, and she moaned into the kiss. Jackson hoisted her off her feet and bore her to the couch, where he sat down with Lily straddling him. He stroked her cheeks with his fingers and resumed kissing her passionately. Their lips continued interlocking and massaging each other. No sooner would one kiss end than another would begin.

Jackson and Lily's last coherent thought was _I could get used to this._


End file.
